Greatest Hits
by Allen92909
Summary: ONE SHOT! Sam is taken and forced into a deep sleep where he is reliving all of his greatest memories. Dean goes after him in an effort to save him before the supernatural son of a bitch can kill Sammy. Can he get there in time? Can he wake Sam?
Greatest Hits...

 **ONE SHOT! Sam is taken and forced into a deep sleep where he is reliving all of his greatest memories. Dean goes after him in an effort to save him before the supernatural son of a bitch can kill Sammy. Can he get there in time? Can he wake Sam?**

 **I have no set time in mind for this story, but will say that it does take place after Castiel gets his grace back and before he says 'yes' to Lucifer.**

 **DISCLAIMER: I do not own Supernatural or the Winchesters.**

Dean made his way down into the nasty, dirty sewer and gagged at the stench that filled his nostrils. On instinct, he covered his nose with his hand, the one holding the flashlight, trying to block out the smell. Why did the supernatural always have to hide out in sewers? He took a deep breath and focused on breathing strictly through his mouth so he could move his hand from his nose and properly aim the flashlight. He had to be on guard for the creature that had Sammy and more so, he had to be able to see. He tightened his grip on his machete in the other hand and began to move slowly through the slosh that went up to his ankles.

He walked down a long corridor of the sewer before it veered to the left. He followed that a ways before he found an opening to some kind of room. There was a step up into the room, so it was void of any sewer slosh. Candles cast an eery glow throughout the room and Dean could see a shadow moving along a far wall. His eyes followed the shadow to a creature that was hovered over a table. He moved in closer to get a better look, hiding behind a column near the center of the concrete room.

On the table laid his brother. Sam looked to be unconscious. The creature, who resembled a human (and was anything but), had his hands on the each side of Sam's head. There was an eery white glow forming around the hands, shifting into his brother at his temples. Dean resisted the urge to go hacking at the damn thing, knowing that it was too close to Sammy and he couldn't risk injuring his brother. He waited a moment.

The creature removed it's hands from Sam's head, the glow dissipating. Sam moaned, his body shifting slightly. Seemingly upset at it's victim's slight movement, it tried to rouse Sam. When it was content that Sam didn't wake, it raised it's hands again to his head. This time the glow emanating from them was a crimson red.

Dean wasn't sure what that meant. Truth be told, he was hunting half cocked. Sam was the one who had done all the research on their current case. Sam would have known the significance of the white versus the red glow, but he had no idea. Sam hadn't had time to inform him before the younger hunter was taken by the damn thing. The whole thing happened while they were on the phone discussing the case and Dean was lucky enough to be able to track Sam's phone to the nearest sewer entrance. So, he had decided it was now or never. He stepped out from behind the column. "Hey, douche bag." He had already tucked away the flashlight, both hands griping the machete tightly.

The creature turned around quickly before it's hands could inflict any more of it's power on Sam. It hissed and lunged at Dean. It had a strength that he wasn't expecting as it forced him back when it's hands shoved hard into his chest. The force sent him crashing against the column. The machete flew free of his hands, clamoring to the ground a few feet away. Though winded from the force of his back striking the column, he tried to shift around the creature as it came at him again. He swirled around and lunged for the machete. The creature snarled and turned angrily at him, but Dean was too quick. He swung the machete with all his strength, aiming for the throat. It tore through the creatures throat and severed the head. The creatures body slumped to the ground, the head rolling a few feet away from it.

Dean swallowed hard as he evened his breathing and turned to his brother who laid lifeless on the table just mere feet from him. "Sam?" He moved to the table. He shook Sam's shoulder a couple of times. "Sammy?" _Oh god, he's not waking._ "Come on, dammit." He took a deep breath and tried to keep himself from panicking. Two fingers went to Sam's neck. _Ok, he's got a pulse._ He could see that Sam was breathing. _Ok, good._ He was worried that he couldn't wake Sam, but knowing he had a steady pulse and was breathing ok did ease his mind a little. Now he just had to figure out how to get Sam out of that sewer.

He sighed, knowing full well that the best way to get Sam out was to call Cas and have him help. He pulled out his cell phone and hit Cas' speed dial. The angel answered quickly.

" _Dean?"_ He had a worried tone to his voice.

"Hey, I need you to zap here and help me get Sammy back to the motel room." Dean explained.

" _You went after him alone, didn't you?"_ Cas asked, a bit of anger in his voice. _"I told you to wait for my arrival."_ Dean had left him a voicemail about the case they were working. It was only when Cas had returned the call that he learned Sam had been taken.

"Sorry, Cas, but Sam's life was on the line." Dean tried to defend himself, even though it would have only taken Cas a moment to zap to him with his angelic powers.

" _Did you at least read the information that Sam had here on this psychic vampire?"_ Cas was still a bit angered.

He hadn't had time to go back to the motel room and read any of Sam's info. "Can you just get your feathery ass over here?" Dean knew they couldn't afford to sit around talking and arguing. They had to help Sam as soon as possible. "We're in the sewers off of 5th and Walnut."

" _Fine."_ The line went dead a moment later as Cas immediately formed in front of him.

"He won't wake up and I can't carry him." Dean said. _Damn Sam for growing into a frickin' sasquatch._

Castiel approached the brothers. He placed his hands on each one and effortlessly teleported the three of them back to their motel room on the outskirts of Buffalo, New York.

Dean swayed for a moment, realizing they were already back in the room. He fought the little bout of nausea that crept into the pit of his stomach. Damn, he didn't think he'd ever get used to traveling like that. He turned to the beds, eyes seeking out his brother's still form.

Cas stood next to the bed, eyes fixed on Dean. "Did the creature touch Sam?" He asked.

"Uh, I..." Dean stammered, trying to get the words out. "I found them in the sewer and that thing had his hands on Sam's head and they were, they were glowing..."

"What color?" When Dean took off without bothering to wait for him, he'd had time to read over Sam's research and knew that color was a very important factor here. "It's very important to know what color."

Dean eyes snapped from Sammy to Cas. "The first time it was gold, but then it pulled away for a minute and when it went back for Sam, it was red." Dean answered. "I stopped it before it could touch him again though."

"Ok, that's very good Dean." Cas replied.

Dean looked at him confused. "How on Earth is that a good thing?" He asked.

"It means that the vampire has not been able to feed on your brother." Cas explained.

Yes, that was good. "Ok, but you can heal him or whatever right? Work some mojo on him?" Dean shot back.

"I'm afraid I can't, Dean." He could see that Dean was about to question him so he added. "Sam is simply asleep. I cannot use my powers to wake him."

"I don't understand." Dean said. "I can't even wake him, so there's gotta be something you can do."

"If you had read the information your brother left..." Cas couldn't even finish his sentence before Dean cut in.

"Alright, I get it." He shot back. "I was stupid to run off without all the facts, but come on man..."

"Dean, the psychic vampire releases a white energy to put it's victim into a deep sleep, where their best memories play on a loop." Cas started explaining. "Then, it emits a red energy which warps and twists their memories into nightmares so it can feed on the torment and fear of their victims. It seems that all the creature was able to do was put your brother into a deep sleep."

"This helps us wake him how?" Dean was relieved that the creature had not gotten the chance to warp Sam's memories, but how were they supposed to wake him?

"I believe you may be able to wake him." Cas said, continuing when Dean raised his eyebrows to question how. "I believe that if you can somehow get inside his mind, than perhaps you could wake him from there."

"Wait, how am I supposed to get..." He stopped for a second. "Can you teleport the impala here?"

Cas looked at him in confusion. "How is the car going to help you with Sam?"

"No, it's what's in the car." Dean replied. "I think I can use some african dream root to get into Sammy's mind and we have a little in the trunk of the impala."

In the blink of an eye, the angel was gone and back again, holding a jar in his hand. "Is this what you were referring to?" He held it out to Dean.

"Yeah, thanks." He said, taking the jar. "Do you really think I have a chance at waking him this way?"

"I'm not entirely sure, but it seems to be the most feasible way." Cas answered.

Dean walked over to Sam and plucked one of his hairs. He uncapped the jar and dropped it in. :Ok, here goes nothing." He gulped the contents of the jar and made an eww face before setting the jar on the nightstand and laying on the bed across from his brothers. He sat up quickly. "Cas, I need you to punch me."

Cas looked confused again. "Dean, I can't..."

He cut him off. "This stuff doesn't work very quickly, so I need you to jump start it by knocking me out." He explained.

"I don't think that I can..." Cas tried to argue. He didn't want to hit his friend.

"Just do it." Dean ordered.

"I'm very sorry, Dean." Cas replied, before his fist met with Dean's face. He tried to aim his punch off center, not wanting to break Dean's nose. As it was, his friend was going to have one nasty black eye when he woke up.

Dean was out on impact and fell back quickly into the pillows. Not a moment later, he opened his eyes...or his subconscious did anyways. He looked around, though darkness surrounded him. He took a step forward, his hands out and trying to feel for something, anything. _What the hell is going on here?_ He expected to find himself in a dream or a memory of Sam's. He was supposed to be reliving his best memories. Dean scoffed at that. He'd already seen his best memories when they visited Sam's version of heaven...times when Sam was free of his family, free from the burden of hunting and saving people. He wasn't exactly anxious to see all of that again. It nearly broke his heart the first time to see how little Sam valued his family.

He spotted something out of the corner of his eyes and whirled around. A vision began to play out before his eyes. He watched in confusion as a seven year old version of himself sat on a bed in a dingy motel room, his three year old brother crying next to him. This wasn't anything he remembered.

 _John walked over to the bed. "It was just a damn dream kiddo. Go back to sleep." He said to his youngest son. He eyed Dean. "Hold down the fort for a couple hours, I'm heading over to the bar across the street for a couple of drinks." He turned and left, Dean scurrying after him to lock the doors and fix the salt lines across the threshold._

 _Sam was still crying, his body trembling as he curled his knees up into his chest and folded his arms around them. "Aw, come on Sammy. It's ok." Dean tried to assure him, walking back to the bed and climbing in next to him._

" _I just want Daddy to hug me and, and..." Sam stuttered._

" _Oh man, it must have been a really bad dream than huh?" Dean asked. "Here..." He pulled Sammy into his arms._

" _Does Daddy love us?" Sam asked._

 _Dean looked at him confused, as if his brother had just asked a ridiculous question. "Of course he does."_

" _Why does he always leave?" Sam was still crying, holding onto Dean as if his life depended on it. Even at only three years old, Sammy was a very smart kid and he was very observant too._

" _He doesn't always..." Dean stopped himself, knowing that what he was about to say was a lie. "I, I don't know Sammy, but I can promise you this...I'll never leave you, ok?" Sammy looked up at him so he continued. "I'll always be here for you, whatever you need."_

 _Sam tried to dry his tears. "You promise?"_

" _Yeah, I promise." Dean answered. "You're my little brother and I'll always have your back. I love ya, Sammy."_

 _Sammy had a huge grin on his face, hugging his brother just a little tighter. "I love you too, Dean."_

Just as quick as the vision, or memory had come, it was gone. Dean looked around again, waiting to see if anymore would come.

 _Bang!_

 _Bang!_

Dean whipped around, facing another memory.

 _Bang!_

 _Bang!_

 _Sam aimed the gun again, hitting the target out in the field ahead of him. He looked to be about thirteen or fourteen now._

 _Bang!_

 _Bang!_

 _He lowered the gun and looked out over the targets to see if he'd hit any of them. He'd hit each one and all but one was a center hit. He tried to reel in his excitement as he turned to face his Dad who'd been trying to teach him for couple years now how to shoot a gun properly._

 _John smiled and ruffled his youngest sons hair, much to Sam's dismay. He hated when anyone messed with his hair. "It's about time. You did good, kiddo. I'm proud of you." He took the gun from Sam. "Now what do you say we go to that little pizza place in town you like so much, the one with that garden pizza or whatever the heck that is?"_

" _Really? You hate that place." Sam was surprised at his Dad's offer._

" _But you don't and you've earned it." He was still beaming at his son's achievement. Sam had a been a slow learner when it came to his hunter training, especially when it came to guns. He was finally able to do what Dean was doing at ten years old._

" _What about Dean?" Sam asked. Dean didn't care for the place either._

" _He's not here now, is he?" John shot back. "Come on, we've got some celebrating to do." He had his arm around Sam as they walked back to the impala. He had a proud look on his face. If one didn't know any better, you'd think his son just cured cancer or won the nobel peace prize. No, he'd only just shot a gun a few times at a target and was finally hitting the damn thing and getting center shots in at that. It's not really something most parents strive for their children to do, much less to do well._

Dean remembered that day. He'd spent the afternoon with some girl that he's long forgotten. He remembered his Dad walking into the apartment they were renting, smiling from ear to ear and bragging about how Sam had hit all the targets during practice. Hell, even he was proud of Sammy that day. Sam was always book smart and always had an easy go at school, which is where Dean lacked a bit, but he always had a hard time when it came to the physical training their Dad put them through. Some days it seemed like their Dad was pushing Sammy just a bit too much and it was mostly due to the fact that he expected his youngest son to catch on like Dean had. So, this was a big moment between Sam and their Dad.

 _Man, if these were some of Sam's best memories, why weren't these the ones in his heaven?_ Dean didn't understand why these memories weren't in Sam's heaven. These were supposed to be some of his best. Before he could give it more thought a couple more memories flew past him. He was only able to catch a glimpse, but in one memory he could distinctly see himself and a younger Sam on the hood of the impala watching fireworks that they'd bought illegally and set off in an old field. He had another quick glimpse at a memory of he and Sam watching a Die Hard Marathon at Bobby's house when they were older. Apparently, none of these memories were in chronological order.

The next memory took place in Sam's apartment near Stanford.

 _Jess straddled Sam on the bed in their bedroom, wearing nothing but a lacy bra and panties._

Dean could easily see where this was going, so he turned away, not wanting to seem like some kind of pervert who gets off on watching his little brother fuck someone. When he realized they weren't making love just yet, he turned back when Jess started speaking.

 _Jess sighed and leaned down so her head rested on Sam's chest. "You can't seriously be too tired." She said, sounding a little disappointed._

 _Sam immediately wrapped his arm around her protectively, as he always did lately...seemingly afraid that if he didn't, she might perish. "It's not that." He tried to assure her. "It's just that it's been a stressful week...what with the LSATS and everything else going on."_

 _She let out a soft smirk. "Well I can help ease some of that stress." She said in a playful tone._

 _Sam gave her a truly genuine smile. "Yeah, I'm very aware of that." He replied. "You know, I don't think I could have gotten through this week without you."_

 _She raised her head from his chest, their eyes meeting. "Oh is that so." She teased._

" _I don't know what I did to deserve you." He said._

" _Well, I guess you'll just have to spend the rest of your life trying to figure it out." She shot back with a smile as she reached down to kiss him._

 _Before her lips could meet his, he jerked his head out from under her. "Wait, what?" He questioned._

" _I might have found a little something in your underwear drawer." She replied._

 _His eyes darted to the dresser and back to Jess. "No, you weren't supposed to see that."_

" _But I did." She said, pulling back and taking a sitting position next to Sam on the bed."And whenever you get around to asking, I want you to know that the answer is yes."_

 _He turned to Jess with a goofy smile on his face. "Are you serious?" He asked. "I, I was gonna wait until after I got the results from the LSATS, but..."_

 _She cut him off. "Oh, this doesn't mean I don't expect a proposal. I'm expecting something romantic and, and..."_

 _This time he cut her off. He surprised her with a kiss, his arms gently wrapping around her to ease her back onto the bed. "You are so amazing Jess and I love you more than anything." His fingers fiddled with her bra, having it off in mere moments. "I can promise you a very romantic proposal." He gently kissed her neck and trailed down to her breasts._

Dean turned away, not wanting to see what he knew was coming. _So Sammy was gonna propose?_ He had no idea his brother planned to propose and if he'd heard right, Sam had had a ring tucked away in the dresser. He wondered why Sam had never mentioned it. He wondered if Sam still had the ring or if it had been lost in the fire.

While he waited for the memory to finish, he tried to figure out how he was supposed to wake Sam. The memories were playing before him like movies and as far as he could tell, he couldn't interfere with them. _Damn, there has to be a way._ The memory faded and everything was dark for a moment.

 _Alright, here goes nothing._ "Sam, Sammy?" He shouted. "Come on Sam..."

The darkness faltered, light creeping in. It became brighter and brighter until it formed into the backdrop of the latest memory, accept that this memory wasn't like the others. Dean felt like he was standing right smack dab in the middle of it. "Sam?" He tried to whip around in search of his brother, but quickly realized that he was in the driver's seat of the impala.

"Dean, this isn't the way to the motel and Dad said..." Sam started from the passenger seat.

He turned to see a sixteen year old Sammy riding shotgun beside him. "Whoa, what the..." He wasn't sure what was going on. The car swerved and Dean quickly regained himself and aimed the car back in his lane.

"Dad said to get in the car and drive straight back to the motel." Sam finished.

He saw an old boarded up factory ahead, it's parking lot long since void of cars. Dean instantly remembered this moment. He'd taken Sam to the old factory and let him drive the impala for the first time. He'd never driven a car before then. Sam had harped about Dad instructing them to go straight back to the motel while he dealt with the police in regards to a current case they'd been working. Dean was usually quick to follow Dad's orders like a good little soldier, but they'd just breezed passed Sammy's birthday without much celebration because the case took precedence. Now, Sam hadn't gotten his permit yet. He couldn't get it until after his birthday, but that didn't mean Dean couldn't take him somewhere and let him feel what it's like to drive for the first time.

He pulled into the lot and parked, eying Sammy.

"What are we doing here Dean?" Sam asked, a hint of worry in his voice.

"I uh...look, that doesn't matter." Dean replied. "I need you to wake up."

"What?" Sam was clearly confused now.

"Some evil son of a bitch put you in a deep sleep and you're mind is replaying your greatest hits, so to speak and I need you to wake up." He tried to explain.

Sam backed away from Dean, his back connecting with the passenger door. "Dean, I don't know what you're talking about and..."

"Damn it, Sammy." Dean was getting frustrated. "I need you to wake the hell up." His voice raised to a yell. "WAKE UP!"

Sam jerked and the whole scene around them seemed to flash a couple of times before everything went dark again.

Dean eye's opened slowly. He groaned and shifted, realizing he was on something soft. His hand fisted around a scratchy comforter. He knew it instantly as the motel room bedding. He shot up quickly. "Sammy?" His head turned to his brother's bed, only to find it empty.

"He's in the restroom, Dean." Castiel said before Dean could even question where his brother was.

His eyes snapped to Cas who was standing near the doorway. "So he's awake?"

"Yes, he woke up about and hour ago." Cas answered. "He complained of being hungry so I walked down to the diner and grabbed you both some food." He gestured to the table at the front of the room by the big picture room that most motels usually had. There was a brown bag of food, some of it out next to the bag and partially eaten already. "I think I will leave the two of you for now. I'm sure you probably want to talk with Sam alone about some of the things you've seen."

Dean eyed him curiously. "Uh, yeah...thanks Cas, I..." Before he could finish, the angel vanished into thin air. He sighed and walked over to the table to see what food he'd left for them. There was a half eaten caeser salad on the table. He wasn't sure how Sammy could eat all that rabbit food. He opened the bag and found a greasy bacon cheeseburger waiting for him. _Come to papa..._ His hands reached around the burger and he took his first juicy bite.

Sam stepped out from the bathroom and almost stopped when he saw that Dean was awake. He wasn't sure he was ready to talk to Dean yet and he was certain that Dean would want to talk after what he'd seen inside Sam's noggin.

"Hey, Dean." He said.

Dean set down his burger on a napkin. "Hey, glad to see your awake." He shot back, a wad of food in his mouth making him slur a bit.

"Yeah, glad to be awake." Sam sat at the table, Dean sitting across from him as he took another bite of his burger.

"So..." Dean wasn't really sure where to start.

Sam stopped him. "Cas told me you were in my head." Dean cocked his head, ready to retort when Sam continued. "What exactly did you see?"

"Well, that damn supernatural freak was supposed to have your greatest hits playing over and over, but I was pretty sure I'd already seen them in Heaven."

"Dean..." Sam tried interject.

"Only, these weren't the same memories." Dean finished, his arms folding over his chest. He seemed a little confused. "These were all different."

"Dean, what you saw in heaven..." Sam wasn't sure how to explain it to his brother. He'd tried before, right after their little trip, but Dean was too angered to listen to what he really had to say so he just told Dean what he was expecting to hear. Now it was time for the truth though. "Those weren't my best memories. I just let you think that because you wouldn't let my tell you otherwise. You wouldn't let me properly explain and I don't blame you. I don't blame you at all. I screwed up, I've done nothing but screw up and..."

"Sammy? You..." Dean tried to argue.

"No, Dean. It's true." Sam shot back. "I've done a lot of bad things, but I've always had you to bring me back from all that and it hurt me that you could ever think that those memories were my best ones because you weren't in them and you've always been one of the most important people in my life."

"That Thanksgiving, I got sick after I over ate. I guess I just wasn't used all that home cooking. You were the one who nursed me back to health after, while we watched that MacGyver marathon in the motel room because nothing else was on."

Dean thought for a second. He remembered that marathon. He learned some neat tricks from MacGyver that have been pretty useful in hunting. He also nearly blew up the motel room they were staying in because he wanted to see if some of the stuff MacGyver did really worked. Sam kept talking.

"That time in Arizona wasn't all it was cracked up to be. I had no idea what to do without you to guide me. So I hid out in an abandoned house with a dog that just wouldn't go away. I thought things would be better on my own without Dad there pushing me so hard to train and be like you, when I wasn't really like you at all. That's when I realized that it might have been better without Dad, but it wasn't better without you."

"I don't know which memories you saw in my head tonight, but those were the greats. Those were some of my best memories...Dad finally being proud of me or at least showing that he was proud, you and I doing some crazy things, like driving in that old parking lot before I even had my permit when we got that flat tire or shooting fireworks off in that field...moments with Jess."

Dean finally spoke. "Why didn't you tell me about Jess?" He asked. Sam looked confused for a second. "Why didn't you tell me you were gonna propose?"

"What?" Sam looked away and Dean could tell he was trying to keep some of his emotions in check. He took in a deep breath and faced his brother again. Talking about Jess was always hard for him. He loved her so much and it hurt to lose her. "Yeah, I guess that was one of the memories huh?" Dean nodded. "I didn't even have time to do a proper proposal. The ring wasn't much, I mean most of my cash went to books or whatever we needed to get by."

"What happened to the ring?" Dean wondered.

"I guess it got lost in the fire." Sam replied. He took a bite of the salad in front of him. He really didn't want to talk about Jessica. He didn't want to remember all that he'd had with her and lost.

"Sammy, I'm sorry about Jess." Dean said seriously. "I'm sorry you lost her. I know how much you cared about her." And suddenly, he can't remember if he's ever actually said those words to Sam before.

"Yeah, thanks Dean." He fought back a couple of tears, knowing Dean wasn't much for chick flick moments.

"Hey, how bout we head home." Dean suggested.

"Home?" Sam was still getting used to having a place to call home, besides the impala anyways. "Uh yeah, sure. Let's go home." He smiled. It was kind of nice having a place to call home.

"Sam?" Dean asked, as his brother walked to the bed to gather his things up.

Sam turned back. "Yeah?"

"You're not a screw up." He replied. "You've done everything with the right intentions and I can't fault you for that. Anyways, you're my annoying little brother and I'll always have your back. I love you man." He doesn't know why he added in that last part. Hell, he doesn't even remember when the last time was that he'd said the L word to his brother, but he felt like now was the right time. He wasn't big on chick flick moments, but they were practically in one already.

Sam smiled. He couldn't remember the last time Dean had said something so meaningful to him. The only time Dean used the L word lately was when he talked about bacon cheeseburgers or some hot model in a magazine. Dean hasn't said it to him in a long time. "Love ya too, jerk."

Dean grinned. "Yeah, whatever Bitch."

 **So I kind of made up my own little version of a psychic vampire. I've seen every episode, but don't recall if they've done one on the show already. I wanted to see some happier memories in Sam's life, so this is what my mind created. I hope you all liked it. Thanks for reading.**


End file.
